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Water → 1-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester

HRID 523674
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인쇄 미리보기

반응식

HRID 523674 반응식
P(Br)(Br)([Br:3])=O.[CH2:6]([O:10][C:11]([C:13]1[N:14]=[C:15](O)[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[C:18]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:17]=2)=[O:12])[CH2:7][CH2:8][CH3:9].C(=O)(O)[O-].[Na+].O>C(#N)C>[CH2:6]([O:10][C:11]([C:13]1[N:14]=[C:15]([Br:3])[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[C:18]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:17]=2)=[O:12])[CH2:7][CH2:8][CH3:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 178450860HCID 178450860, 화합물

생성물 1

HCID 865954621-Bromo-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester수율 68.2%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

To a solution of 4.59 g of phosphorous oxybromide (16 mmol) in 25 ml of anhydrous acetonitrile were added 1.11 g of 1,4-dihydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (3 mmol) and the mixture was refluxed gently with stirring for 1 h. Then 5.04 g of sodium bicarbonate (60 mmol) were added, followed by the dropwise addition of 8 ml of water. After stirring at ambient temperature for 90 min the mixture was concentrated in vacuo to about one third of its volume, 40 ml of water were added and the mixture was extracted with 30 ml of ethyl acetate. The mixture was filtered by suction. The organic phase was separated, dried over MgSO4, and filtered through a pad of silica gel. Evaporation in vacuo gave 0.885 g of the title compound; 1H NMR (CDCl3): δ=11.84 (s, 1H), 8.21 (d, 1H), 7.91 (d, 1H), 7.40 to 7.55 (m, 6H), 4.46 (t, 2H), 1.84 (m, 2H), 1.48 (m, 2H), 0.98 (t, 3H).

후처리

  1. temperaturethe mixture was refluxed gently
  2. stirringAfter stirring at ambient temperature for 90 min the mixture
  3. concentrationwas concentrated in vacuo to about one third of its volume, 40 ml of water
  4. additionwere added
  5. extractionthe mixture was extracted with 30 ml of ethyl acetate
  6. filtrationThe mixture was filtered by suction
  7. customThe organic phase was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered through a pad of silica gel
  10. customEvaporation in vacuo

출처 및 근거

ORD 기록
ord-db38d78b41ec4875ad3406d31c27fc1c
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09339527B2

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